Organocatalyzed [3+3] Annulations for the Construction of Heterocycles

Abstract

Six-membered heterocyclic systems are widely distributed in many natural products and pharmaceuticals, and the construction of highly functionalized six-membered heterocyclic compounds is an important topic in modern organic synthesis. Organocatalyzed [3+3] annulations represents an important method for assembling a substantial variety of six-membered cycles that contain one or more heteroatoms. This review describes the development of organocatalyzed [3+3] annulations for the synthesis of six-membered heterocycles, including organocatalysis using secondary amines, tertiary amines, phosphines, chiral phosphoric acids and N-heterocyclic carbenes.

1 Introduction

2 Secondary Amine Catalyzed [3+3] Annulations

2.1 Synthesis of Nitrogen Heterocycles

2.2 Synthesis of Oxygen Heterocycles

2.3 Synthesis of Sulfur Heterocycles

3 Tertiary Amine Catalyzed [3+3] Annulations

3.1 Catalysis through Multiple Hydrogen-Bonding Interactions

3.2 Catalysis of Tertiary Amines as Lewis Bases

4 Phosphine-Catalyzed [3+3] Annulations

4.1 Synthesis of Nitrogen Heterocycles

4.2 Synthesis of Oxygen Heterocycles

4.3 Synthesis of Heterocycles Containing Two or More Heteroatoms

5 Chiral Phosphoric Acid Catalyzed [3+3] Annulations

5.1 Synthesis of Nitrogen Heterocycles

5.2 Synthesis of Heterocycles Containing Two or More Heteroatoms

6 N-Heterocyclic Carbene Catalyzed [3+3] Annulations

6.1 Synthesis of Nitrogen Heterocycles

6.2 Synthesis of Oxygen Heterocycles

6.3 Synthesis of Heterocycles Containing Two or More Heteroatoms

7 Conclusion and Outlook

Key words

annulations - heterocycles - organocatalysis - amines - phosphines - chiral phosphoric acids - N-heterocyclic carbenes

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